EP0155470B1 - Wasserunlösliche Monoazofarbstoffe, ihre Herstellung und Verwendung - Google Patents

Wasserunlösliche Monoazofarbstoffe, ihre Herstellung und Verwendung Download PDF

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Publication number
EP0155470B1
EP0155470B1 EP85100923A EP85100923A EP0155470B1 EP 0155470 B1 EP0155470 B1 EP 0155470B1 EP 85100923 A EP85100923 A EP 85100923A EP 85100923 A EP85100923 A EP 85100923A EP 0155470 B1 EP0155470 B1 EP 0155470B1
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EP
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Prior art keywords
formula
carbon atoms
mixtures
dyestuffs
dye
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
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EP85100923A
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German (de)
English (en)
French (fr)
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EP0155470A1 (de
Inventor
Ulrich Dr. Bühler
Horst Dr. Tappe
Manfred Dr. Hähnke
Albert Bode
Kurt Roth
Margarete Boos
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Sanofi Aventis Deutschland GmbH
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Cassella AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0805—Amino benzenes free of acid groups
    • C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
    • C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
    • C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
    • C09B29/0813—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl)

Definitions

  • the invention also relates to mixtures of dyes of the formula 1, where in such mixtures R 1 for a dye component can also be methyl.
  • the invention further relates to the production of these dyes and their mixtures and their use for dyeing hydrophobic fiber materials.
  • Alkyl radicals with 2 to 6 carbon atoms, which represent R 1 can be linear or branched. Examples of such radicals are ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-buti, tert-butyl, n-pentyl, i-pentyl and n-hexyl.
  • Cycloalkyl radicals with 5 or 6 carbon atoms are the cyclopentyl and cyclohexyl radicals.
  • Halogen R 1 is fluorine, preferably chlorine or bromine.
  • Alkyl radicals which are R 2 or R 3 can also be branched. However, at least one of the alkyl radicals which are R 2 and R 3 is preferably linear.
  • Linear alkyl radicals with 1 to 4 carbon atoms which can represent R 2 or R 3 , are, for. As methyl, ethyl, n-propyl and n-butyl.
  • Alkoxy groups with 1 to 4 carbon atoms in the alkoxyalkyl radicals which can represent R 2 or R 3 .
  • R 2 or R 3 e.g. B. methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy or tert-butoxy.
  • alkoxy radicals mentioned can be in any position of the alkyl radical of the alkoxyalkyl group, with the exception of the 1-position, for. B. in an ethyl group in the 2-position, in a propylene group in the 2-or 3-position and in a butyl group in the 2-, 3- or 4-position.
  • alkoxyalkyl groups are 2-methoxyethyl, 2-butoxyethyl, 2-tert-butoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 2- or 3-propoxypropyl, 2-, 3- or 4-methoxybutyl.
  • Preferred alkoxyalkyl radicals are those in which the alkoxy group is attached to the outermost C of the alkyl chain.
  • Cyanalkyl radicals which can represent R 2 and R 3 are 2-cyanoethyl, 3-cyanopropyl- (1), 3-cyanopropyl- (2) and cyanobutyl.
  • R 2 and / or R 3 are cyanoalkyl, preference is given to those in which only one of the substituents R 2 or R 3 is a cyanoalkyl group and the other is one of the defined alkoxyalkyl or, in particular, alkyl groups.
  • Preferred alkyl radicals for R 1 are n-propyl and i-propyl; a particularly preferred alkyl radical R 1 is ethyl.
  • Preferred unsubstituted alkyl radicals R 2 and R 3 are ethyl or propyl.
  • Preferred alkoxyalkyl radicals R 2 and R 3 are alkoxyethyl radicals, in particular the methoxy and ethoxyethyl radicals.
  • a preferred cyanoalkyl radical R 2 or R 3 is the 2-cyanoethyl radical.
  • R 1 is ethyl and R 2 and R 3 independently of one another are linear alkyl having 1 to 4 carbon atoms, in particular ethyl and propyl and R 4 are methyl are particularly preferred.
  • R 1 is methyl, ethyl, chlorine or bromine
  • R 2 is cyanoalkyl, in particular cyanoethyl or R 3 is linear alkyl or alkoxyethyl, in particular ethyl and n-propyl or n-butyl
  • R 4 is hydrogen and in particular means methyl
  • Dyes similar to the dyes according to the invention are already known and are described in EP-PS 25903. It was surprisingly found, however, that the dyes according to the invention in the dyeing behavior on various substrates, in particular in HT dyeing at temperatures below 130 ° C, and in some important fastness properties, for. B. the light fastness, are clearly superior.
  • the dyes according to the invention are preferably prepared by azo dyes of the formula 11 in which R 1 , R 2 , R 3 and R 4 have the meanings given above, X is cyan or Hal and Hal is a halogen atom such as chlorine or in particular bromine, in a manner known per se, for. B. according to the details of DE-OS 1 809 920, DE-OS 1 809 921, GB-PS 1 184 825, DE-AS 1 544 563, DE-OS 2 310 745, DE-AS 2 456 495, DE-AS 2 610 675, DE-OS 2 724 116. DE-OS 2 724 117. DE-OS 2 834 137, DE-OS 2 341 109 of US Pat. No. 3,821 195, subject to DE-OS 2 715 034 or DE-OS 2 134 896 a nucleophilic exchange reaction, the cyanide ion CN ⁇ being used as the nucleophilic agent.
  • Inert organic solvents such as e.g. B. nitrobenzene or glycol or diglycol mono-methyl or mono-ethyl ether or mixtures of such solvents with one another and with tertiary organic nitrogen bases, dipolar aprotic solvents, such as. B. methylpyrrolidone, pyridine, dimethylformamide or dimethyl sulfoxide, dicyandialkylthioether used.
  • dipolar aprotic solvents such as. B. methylpyrrolidone, pyridine, dimethylformamide or dimethyl sulfoxide, dicyandialkylthioether used.
  • water or aqueous systems consisting of water and a water-immiscible (e.g.
  • nitrobenzene) organic solvent preferably in the presence of a wetting or dispersing agent or a known phase transfer catalyst or of water and a water-soluble, inert, are the medium for the exchange reaction organic solvents, such as ethylene glycol or dimethylformamide, are suitable.
  • the reaction temperatures are usually between 20 and 150 ° C.
  • the nucleophilic agent CN 6 is the reaction in the form of an optionally complex metal cyanide, such as. B. an alkali or alkaline earth metal cyanide, zinc cyanide, alkaiicyano zincate or ferrate, but preferably in the form of copper-I-cyanide or a copper-I-cyanide-forming system added.
  • an optionally complex metal cyanide such as. B. an alkali or alkaline earth metal cyanide, zinc cyanide, alkaiicyano zincate or ferrate, but preferably in the form of copper-I-cyanide or a copper-I-cyanide-forming system added.
  • the use of a combination of alkali metal cyanide with copper-I-cyanide has proven particularly successful. the ratio of alkali and copper salt can be varied within wide limits.
  • the common range of the alkali metal cyanide / copper-I-cyanide ratio is 5: 95 to 95: 5.
  • the positive mutual influence of the components can also be determined outside these limits.
  • the dyes of the formula II required for the preparation of the dyes according to the invention can be prepared by adding a diazonium compound of an aromatic amine of the general formula III with a coupling component of the general formula IV wherein R 1 , R 2 , R 3 and R 4 have the meanings given above. is coupled.
  • the diazonium compounds are known in a manner known per se by the action of nitrous acid or other nitrosonium ion-forming systems in a mineral acid or a mineral acid aqueous medium, a lower alkane carboxylic acid, such as, for. B. formic acid. Acetic acid or propionic acid or mixtures thereof. or an organic solution obtained at temperatures from -15 ° C to 40 ° C.
  • the coupling is also carried out in a manner known per se by combining the diazo solution obtained with a solution of the coupling component at temperatures from 0 to 40 ° C., preferably 0 to 25 ° C., in a suitable solvent, such as, for. B. an alkanol having 1 to 4 carbon atoms, dimethylformamide, preferably in water acidified with sulfuric acid, hydrochloric acid or phosphoric acid, or an optionally water-containing lower alkane carboxylic acid or a lower alkane carboxylic acid mixture, optionally also in the presence of an alkanol which is miscible with water to a limited extent. In some cases it may be useful to buffer the pH during the coupling, e.g. B. by adding sodium acetate.
  • the coupling is complete after a few hours and the dye of the formula II can be isolated and dried as usual.
  • the required coupling components of the formula IV can be produced from known commercial products by known processes.
  • Another process for the preparation of the dyes according to the invention is that an amine of the formula V diazotized and on a coupling component of formula IV in which R 2 , R 3 and R 4 have the meanings given above, couples.
  • the diazonium compounds are known in a manner known per se by the action of nitrous acid or other systems which form nitrosonium ions in a mineral acid or a mineral acidic aqueous medium, a lower alkane carboxylic acid, such as, for. B. formic acid, acetic acid or propionic acid or mixtures thereof, or an organic solvent at temperatures from 0 to 40 ° C.
  • the coupling also takes place here in a manner known per se by combining the diazo solution obtained with a solution of the coupling component at temperatures from 0 to 40 ° C., preferably 0 to 25 ° C., in a suitable solvent, such as, for. B. an alkanol with 1 to 4 carbon atoms, dimethylformamide, preferably in water acidified with sulfuric acid, hydrochloric acid or phosphoric acid, or an optionally water-containing lower alkane carboxylic acid or a lower alkane carboxylic acid mixture, optionally also in the presence of an alkanol which is miscible with water to a limited extent. In some cases it may be useful to buffer the pH during the coupling, e.g. B. by adding sodium acetate. The coupling is complete after a few hours and the dye can be isolated and dried as usual.
  • a suitable solvent such as, for. B. an alkanol with 1 to 4 carbon atoms, dimethylformamide, preferably in water acidified with sulfuric acid
  • the dye mixtures according to the invention consist of two or more dyes of the formula I in which R 1 to R 4 have the meanings given above and R 1 can also be methyl when R 2 and / or R 3 are not cyanoalkyl.
  • the mixtures preferably contain at least one component in which R 1 is alkyl having 2 to 6 carbon atoms or cycloalkyl having 5 or 6 carbon atoms.
  • radicals R 4 of the respective individual dyes are the same and the radicals R 1 , R 2 and R 3 are variable within the scope of the above definition.
  • dye mixtures are preferred in which the radicals R 1 , provided that they are different in the individual components and are hydrocarbon radicals, are homologs of a series.
  • the radicals R 2 and R 3 are homologs of a series.
  • Homologs of a number of unsubstituted alkyl radicals or cyanoalkyl radicals differ in the number of methylene groups in the alkyl radical.
  • Homologs of a number of alkoxy-substituted alkyl radicals differ in the number of methylene groups in the alkyl radical or in the alkoxy groups.
  • R 1 can be a hydrocarbon radical or a halogen in the context of the above definition. Mixtures of components in which all R 'are either hydrocarbon radicals or different representatives of the halogen series are preferred.
  • the ratio of the different dyes of general formula 1 vary within relatively wide limits.
  • the minimum weight percentage of a component is 10% and the maximum weight percentage 90%.
  • a quantitative ratio of 70:30 to 30:70 is preferred, ie the proportion by weight of a dye is 30 to 70%.
  • Dyes and dye mixtures according to the invention in which two or more of the preferred features mentioned above are present are particularly preferred.
  • the dye mixtures according to the invention can be prepared by various processes. Firstly by mixing at least two individual dyes of the formula I, preferably with the addition of dispersants. This mixing process takes place at temperatures from 0 to 190 ° C., expediently in suitable mills, for example ball and sand mills, and kneaders, but can also be effected by mixing by hand or by stirring into dispersants or dye liquors.
  • Such dispersing agents are those of an anionic or non-anionic nature.
  • Anionic dispersants which may be mentioned are condensation products of naphthalene, formaldehyde and sulfuric acid and lignin sulfonates.
  • Nonionic dispersants are e.g. B. described in DE-OS 27 57 330.
  • the individual dyes of the formula I are known and z. B. described in German Patent 17 94 402 and in German Offenlegungsschrift 30 09 695.
  • Another process for the preparation of the dye mixtures according to the invention is that an amine of the formula V diazotized and on a mixture of at least two different coupling components of the formula IV in which R 2 , R 3 and R 4 have the meanings given above and R 4 is preferably identical in all coupling components.
  • composition of the mixture of the coupling components is chosen so that the desired dye mixtures according to the invention are formed.
  • the diazotization and coupling is carried out in a manner known per se, as is customary for the production of individual dyes.
  • dye mixtures are to be produced whose components differ with respect to R 1 , then instead of a single amine of the formula V, a mixture of such amines is diazotized, the individual components of which differ in a corresponding manner with respect to R 1 .
  • both mixtures of the amines V and mixtures of the coupling components IV can also be used.
  • the new dye mixtures can be prepared by mixing in dye mixtures consisting of at least two dyes of the formula VI exist in which Z is cyan or halogen and Hal is halogen, preferably bromine, and R ', R 2 R 3 and R 4 have the meanings given above, in a manner known per se, exchanging halogen for cyan, as z. B. is described in GB-PS 1 125 685 for single dyes.
  • the composition of the mixture of the dyes of the formula VII is chosen in this way. that dye mixtures according to the invention arise.
  • dye mixtures which have been heated to temperatures of at least 80 ° C. in the course of their preparation, or to contain dye mixtures which consist of mixed crystals, or mixed crystals which are formed from two or more of the dyes of the formula I.
  • Dyestuff mixtures which in the course of their manufacture at temperatures of at least 80 ° C, z. B. to temperatures of 80 to 190 ° C, especially 90 to 150 ° C, preferably 100 to 140 ° C, can be prepared by using the individual dyes in bulk or preferably in a dispersing agent, such as. B. water, heated to the temperatures mentioned for 0.5 to 3 hours, then cooling, usually isolated and then mixed together. The heating can optionally also be carried out as part of a recrystallization of the individual dyes. The heating in water to temperatures above 100 ° C is carried out in a closed vessel. When heating in a dispersing agent, the addition of one or more of the dispersing agents specified below can be expedient.
  • Dye mixtures according to the invention consisting of mixed crystals or containing mixed crystals can also be prepared by adding a mixture of at least two separately prepared, different dyes of the formula I which, for. B. in the German patent specification 1,794,402 or in the German Offenle supply specification 30 09 695 are described, dissolves and leads to crystallization or precipitation.
  • organic solvents such as dimethylformamide, dimethyl sulfoxide, chlorobenzene, o-dichlorobenzene, toluene etc. are suitable. Mixtures of different solvents can also be used. The dissolution is advantageously carried out at the boiling point of the solvent or solvent mixture.
  • Mixed crystals then crystallize on cooling. Instead of cooling, the mixed crystals can also be precipitated, i.e. H. by adding a solvent in which the dye is less soluble can be deposited.
  • Mixed crystals are also particularly preferably obtained when the above-mentioned exchange of halogen for cyan is carried out at temperatures of at least 80 ° C. in a mixture consisting of dyes of the formula IV.
  • the mixed crystal formation can preferably also be carried out by mixing a mixture of at least two separately prepared, different dyes of the formula I in one. solvent or dispersing agent warms up, whereby only a partial down to a vanishingly low resolution takes place, and thereby converts the mixture into mixed crystals.
  • Water at temperatures of 80 to 190.degree. C., in particular 90 to 150.degree. C., preferably 100 to 140.degree. C. has proven to be a particularly suitable solvent or better said dispersion medium for such a conversion of the dye mixtures into mixed crystals.
  • the heating is carried out in an autoclave at temperatures which can no longer be reached in an open vessel.
  • the addition of one or more solubilizers is expedient.
  • Such a mediator is such.
  • the conversion of the dye mixtures into mixed crystals is particularly preferably carried out by heating in water to the above-mentioned temperatures with the addition of one or more emulsifiers and / or dispersants.
  • Suitable dispersants are e.g. B. anionic or nonionic dispersants, which can also be used together.
  • Anionic dispersants are e.g. B. condensation products from aromatic sulfonic acids and formaldehyde, in particular condensation products from alkylnaphthalenesulfonic acids and formaldehyde, condensation products from optionally substituted phenol with formaldehyde and sodium bisulfite, alkali metal salts from condensation products from optionally substituted phenol, naphthalene or naphtholsulfonic acids, formaldehyde and sodium bisulfalide from optionally substituted alkali metal alkali metal Phenolsulfonic acids, formaldehyde and urea as well as alkali metal salts of ligninsulfonic acids, alkyl or alkylarylsulfonates, as well as alkyl aryl polyglycol ether sulfates.
  • Nonionic dispersants or emulsifiers are e.g. B. reaction products of alkylene oxides, such as. B. ethylene or propylene oxide with alkylatable compounds, such as. B. fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, arylalkylphenols, arylalkylarylphenols and carboxylic acid amides, such as. B. addition products of 5 to 10 ethylene oxide units on C 8 -C, o alkyl phenols.
  • alkylene oxides such as. B. ethylene or propylene oxide
  • alkylatable compounds such as. B. fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, arylalkylphenols, arylalkylarylphenols and carboxylic acid amides, such as. B. addition products of 5 to 10 ethylene oxide units on C 8 -C, o alkyl phenols.
  • the conversion of the dye mixtures into mixed crystals by heating in water is usually complete after 0.5 to 10 hours, preferably 1 to 3 hours.
  • the dyes and dye mixtures according to the invention are individually or in a mixture with other disperse dyes particularly suitable for dyeing and printing hydrophobic synthetic materials.
  • Suitable hydrophobic synthetic materials are: cellulose-2 1/2 acetate, cellulose triacetate, polyamides and particularly high molecular weight polyesters, such as, for. B. polyethylene glycol terephthalate.
  • the dyes according to the invention are preferably used for dyeing and printing materials made from high molecular weight polyesters, in particular those based on polyethylene glycol terephthalates or their mixtures with natural fiber materials, or materials made from cellulose triacetate. These materials can be in the form of flat or thread-like structures and z. B. be processed into yarns or woven or knitted textiles.
  • the dyeing of the said fiber material with the dyes according to the invention is carried out in a manner known per se, preferably from an aqueous suspension, if appropriate in the presence of carriers, between 80 to approx. 110 ° C.
  • the printing pastes containing printing pastes according to the invention are treated with HT steam, pressurized steam or dry heat to fix the dye, optionally in the presence of a carrier, at temperatures between 80 to 230 ° C. In this way, very strong red dyeings and prints are obtained with very good fastness properties, in particular very good light fastness and low sensitivity to reduction.
  • the dyes according to the invention are also suitable for dyeing the hydrophobic materials listed above from organic solvents by the methods known here and for dyeing in bulk.
  • the dyes according to the invention should be as finely divided as possible.
  • the fine distribution of the dyes is carried out in a manner known per se by slurrying the dye obtained in manufacture together with dispersants in a liquid medium, preferably in water, and exposing the mixture to the action of shear forces, the dye particles originally present being mechanical are crushed to such an extent that an optimal specific surface is achieved and the sedimentation of the dye is as low as possible.
  • the particle sizes of the dyes are generally between 0.5 and 5 1 1m, preferably about 1 wm.
  • the dispersants used in the grinding process can be nonionic or anionic.
  • Nonionic dispersants are e.g. B. reaction products of alkylene oxides, such as. B. ethylene or propylene oxide with alkylatable compounds, such as. B. fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols and carboxamides.
  • Anionic dispersants are, for example, lignin sulfonates, alkyl or alkylaryl sulfonates or alkyl aryl polyglycol ether sulfates.
  • the dye preparations thus obtained are said to be pourable for most applications.
  • the dye and dispersant content is therefore limited in these cases.
  • the dispersions are adjusted to a dye content of up to 50 percent by weight and a dispersant content of up to about 25%.
  • the dye content is usually not below 15 percent by weight.
  • the dispersions can also contain other auxiliaries, e.g. B. those that act as oxidizing agents such. B. sodium m-nitrobenzenesulfonate or fungicidal agents, such as. B. sodium o-phenyl phenolate and sodium pentachlorophenolate.
  • auxiliaries e.g. B. those that act as oxidizing agents such. B. sodium m-nitrobenzenesulfonate or fungicidal agents, such as. B. sodium o-phenyl phenolate and sodium pentachlorophenolate.
  • the dye dispersions obtained in this way can be used very advantageously to prepare printing pastes and dyeing liquors. They offer special advantages e.g. B. in the continuous process, in which the dye concentration of the dye liquors must be kept constant by continuous dye feed into the running apparatus.
  • Powder settings are preferred for certain areas of application. These powders contain the dye, dispersant and other auxiliaries, such as. B. wetting, oxidizing, preserving and dedusting agents.
  • a preferred manufacturing process for powdered dye preparations is that the liquid is removed from the liquid dye dispersions described above, e.g. B. by vacuum drying, freeze drying, by drying on drum dryers, but preferably by spray drying.
  • the required amounts of the dye settings which have been prepared in accordance with the above information are diluted with the dyeing medium, preferably with water, to such an extent that a liquor ratio of 1: 5 to 1:50 results for the dyeing.
  • further dyeing aids such as dispersing, wetting and fixing aids, are generally added to the liquors.
  • the required amounts of the dye settings are used together with thickeners, such as. B. alkali alginates or the like, and optionally other additives such. B. fixing accelerators, wetting agents and oxidizing agents. kneaded into printing pastes.
  • a) 45.2 g of the dye of the formula are in a suspension of 100 ml of dimethyl sulfoxide and 20 g of copper-I-cyanide at 75 to 80 ° C. entered and stirred for 1/2 hour at this temperature. Then the temperature is raised to 110 ° C. for 1/2 hour and the mixture is then slowly stirred cold, suction filtered, washed with 45 ml of dimethyl sulfoxide, 7.5% aqueous ammonia solution and water and dried under reduced pressure.
  • a dye preparation which is ready for dyeing is obtained by a finish process customary in practice by aqueous bead milling with a customary dispersant based on lignin sulfonate and subsequent spray drying.
  • 1.2 g of the dye preparation thus obtained are dispersed in 2,000 g of water.
  • the dispersion is adjusted to a pH of 4-5 with acetic acid and 4 g of anhydrous sodium acetate and 2 g of a commercial dispersant based on a naphthalenesulfonic acid-formaldehyde condensate are added.
  • 100 g of a polyester fabric based on polyethylene glycol terephthalate are introduced into the dye liquor thus obtained and dyeing is carried out at 120 ° C. for 30 minutes.
  • Example 1c If the dyeing described in Example 1c is carried out with the addition of a commercially available dyeing accelerator (carrier) at a dyeing temperature reduced to 98-100 ° C. and a dyeing time increased to 60 minutes, an equivalent dyeing with equivalent dye bath exhaustion is obtained.
  • a commercially available dyeing accelerator carrier

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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EP85100923A 1984-02-07 1985-01-30 Wasserunlösliche Monoazofarbstoffe, ihre Herstellung und Verwendung Expired EP0155470B1 (de)

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DE19843404130 DE3404130A1 (de) 1984-02-07 1984-02-07 Wasserunloesliche monoazofarbstoffe, ihre herstellung und verwendung
DE3404130 1984-02-07

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EP0155470A1 EP0155470A1 (de) 1985-09-25
EP0155470B1 true EP0155470B1 (de) 1987-05-27

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EP (1) EP0155470B1 (enrdf_load_stackoverflow)
JP (1) JPS60181165A (enrdf_load_stackoverflow)
DE (2) DE3404130A1 (enrdf_load_stackoverflow)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3705223A1 (de) * 1986-07-30 1988-02-04 Bayer Ag Azofarbstoffe
DE3820191A1 (de) * 1988-06-14 1989-12-21 Bayer Ag Verfahren zum faerben thermoplastischer kunststoffe in der masse
DE3831356A1 (de) * 1988-09-15 1990-03-29 Cassella Ag Wasserunloesliche monoazofarbstoffe, ihre herstellung und verwendung sowie mischungen aus diesen monoazofarbstoffen
DE4106323A1 (de) * 1991-02-28 1992-09-03 Cassella Ag Verfahren zum faerben von polyester und polyesterhaltigen textilmaterialien
US5428137A (en) * 1992-01-31 1995-06-27 Orient Chemical Industries, Ltd. Monoazo liquid dye and solutions thereof
JP2986609B2 (ja) * 1992-05-14 1999-12-06 オリヱント化学工業株式会社 アゾ液体染料およびそれを含むインキ組成物

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US3962209A (en) * 1962-03-09 1976-06-08 Bayer Aktiengesellschaft Process for preparing azo dyestuffs with ortho-azo cyano groups by cyano exchange of metal cyanides and halo dyestuffs
DE1963735C3 (de) * 1969-12-19 1978-06-01 Bayer Ag, 5090 Leverkusen Monoazofarbstoffe und Verfahren zum kontinuierlichen Färben von synthetischen Fasermaterialien
GB1559562A (en) * 1977-03-15 1980-01-23 Bayer Ag Azo compounds
DE2937329A1 (de) * 1979-09-14 1981-04-02 Bayer Ag, 5090 Leverkusen Azofarbstoffe sowie deren herstellung und verwendung

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DE3560198D1 (en) 1987-07-02
EP0155470A1 (de) 1985-09-25
DE3404130A1 (de) 1985-08-08
JPH0569141B2 (enrdf_load_stackoverflow) 1993-09-30
JPS60181165A (ja) 1985-09-14

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